Note: Descriptions are shown in the official language in which they were submitted.
~3V0915
-- 1 --
"HERBICIDAL METHOD USING DIFLUFENICAN''
The present invention relates to new herbicidal
compositions comprising N-(2,4-difluorophenyl)-
2-(3-trifluoromethylphenoxy)nicotinamide of formula I
depicted hereinafter, which is disclosed in the
specification of British Patent No. 2087887B as a pre-
and/or post-emergence herbicide, and to their use in
agriculture.
The phenoxyalkanoic acid herbicides and mixtures
thereof, especially 2,4-D [2,4-dichlorophenoxyacetic
acid], 2,4-DP (also known as dichlorprop)
~(+)-2-(2,4-dichlorophenoxy)propionic acidJ,
MCPA E4-chloro-2-methylphenoxyacetic acid] or
CMPP (also known as mecoprop)
[(+)-2-(4-chloro-2-methylphenoxy)propionic acid], are
used on a large scale for post-emergence broad-leaf
weed control in cereal crops.
It iB to be understood that where in this
specification reference is made to "a phenoxyalkanoic
acid herbicide" it is intended to refer, where the
context so permits, to the phenoxyalkanoic acid
herbicide in the form of the parent acid (acid
equivalent), or an agriculturally acceptable salt (or
mixture of salts) or ester (or mixture of esters)
thereof, preferably a metal or amine salt or a
straight- or branched-chain alkyl ester thereof
containing from 1 to 10 carbon atoms in the alkyl
moiety which is optionally substituted by Cl 6-alkoxy
13(~0915
group(s), or a mixture thereof. The invention
embraces the use of a phenoxyalkanoic acid in the form
of a herbicidally active enantiomer or mixture of
enantiomers thereof
Owing to short-lived residual activity in the soil
the phenoxyalkanoic acid herbicides do not reliably
control the weeds which emerge after application.
As a result of research and experimentation it has
now been discovered that the use of the compound
N-(2,4-difluorophenyl)-2-(3-trifluoromethylphenoxy)-
nicotinamide (hereinafter referred to as diflufenican)
in combination with a phenoxyalkanoic acid herbicide
adds to their c~pabilities in controlling a wide
spectrum of broad-leaf weeds by both foliar activity
and residual soil activity.
In addition to this it has been found that the
combined herbicidal activity of combinations of
difluenican with the phenoxyalkanoic acid herbicide
against certain broad-leaf weed species is greater than
expected when applied post-emergence (e.g, as a
post-emergence spray), i.e. the herbicidal activity of
combinations of diflufenican with the phenoxyalkanoic
acid herbicide showed an unexpected degree of synergism
~as defined by P.M.L. Tammes, Netherlands Journal of
Plant Pathology, 70 (1964), pp 73-80 in a paper
entitled "Isoboles, a graphic representation of
synergism in pesticides"~.
13~915
-- 3 --
The remarkable synergistic effect of the mixture
applied post-emergence gives improved reliability of
control of weed species occurring in cereal cultures
and allows for a reduction in the amount of active
ingredient employed.
Accordingly the present invention provides a method
for the control of the growth of weeds at a cereal crop
locus which comprises applying to the locus,
post-emergence of the weeds, (a) a phenoxyalkanoic acid
herbicide, preferably a compound of general formula II
wherein the symboI A represents a straight- or
branched-chain alkylene group containing from l to 6
carbon atoms, Rl represents a halogen, preferably
chlorine, atom, a straight- or branched-chain alkyl
group containing from l to 6 carbon atoms, preferably
the methyl group, or a straight- or branched-chain
alkoxy group containing from l to 6 carbon atoms, R2
represents a halogen, preferably chlorine, atom and n
is the integer l or 2, [more preferably MCPA or CMPP],
or an agriculturally acceptable salt or ester thereof,
preferably a metal or amine salt or a straight- or
branched-chain alkyl ester thereof containing from l to
lO carbon atoms in the alkyl moiety which is optionally
substituted by Cl_6-alkoxy group(s), or a mixture
thereof and (b) diflufenican,
i3~0915
-- 4 --
Preferably the application rates are from 125 to 250~ g
acid equivalent (a.e.~/ha of (a) [preferably from 125
to 500 g a.e./ha for MCPA and from 500 to 2500 g
a.e./ha for CMPP~ and from 25 to 250 g/ha of (b), in a
ratio of (a) to (b) of 20:1 to 1:2 w/w for MCPA and
from 100:1 to 2:1 w/w for CMPP. The method of the
invention may be used to control a broad spectrum of
weed species in cereal crops, e.g. wheat or barley by
application pre- or post-emergence of the crop without
significant permanent damage to the crop. The
combined use described above provides both foliar and
residual activity.
Preferred compounds of general formula II are
2,4-dichlorophenoxyacetic acid,
(+)-2-(2,4-dichlorophenoxy)propionic acid,
4-~2,4-dichlorophenoxy)butyric acid,
4-(4-chloro-2-methylphenoxy)butyric acid,
4-chloro-2-methylphenoxyacetic acid or
(-)-2-(4-chloro-2-methylphenoxy)propionic acid, the
last two of which are known respectively as MCPA and
CMPP (or mecoprop), and more especially the
(+)(or R)-enantiomer of CMPP.
13~g~S
-- 5 --
According to a preferred feature of the invention
there is provided a method for the control of weeds at
a cereal crop locus which comprises the application to
the locus, post-emergence of the weeds, of (a) R-CMPP or
an agriculturally acceptable salt or ester thereof,
preferably a metal or amine salt or a straight- or
branched-chain alkyl ester thereof containing from 1 to
10 carbon atoms in the alkyl moiety which is optionally
substituted by Cl 6-alkoxy group(s), and (b)
diflufenican at application rates of from 250 to 1250 g
acid equivalent (a.e.)/ha of (a) and from 25 to 250
g/ha of (b), in a ratio of 50:1 to 1:1 w/w of (a) to
(b).
Preferred esters of the compounds of general
formula II are 2-butoxyethyl, isooctyl or isopropyl.
Preferred salts of the compounds of general formula
II are those with sodium, potassium or dimethylamine.
.. . . . . ... , . . . . .. .. .. .... . , .. . ...... ~ . . . . . . . . .. . . .. .. . ..... . .
~3~0~15
-- 6 --
By the term 'post- emergence application', unless
otherwise specified, is meant application to the aerial
or exposed portions of the weeds which have emerged
above the surface of the soil. By the term 'foliar
activity' is meant herbicidal activity produced by
application to the aerial or exposed portions of the
weeds which have emerged above the sur~ace of the
soil. By the term 'residual activity' is meant
herbicidal activity produced by application to the soil
in which weed seeds or seedlings are present before
emergence of the weeds above the sur~ace of the soil,
whereby seedlings present at the time of application or
which germinate subsequent to application from seeds
present in the 80il, are controlled.
Weeds that may be controlled by the method
include:- from broad-leaf weeds, Abutilon theophrasti,
Amaranthus retroflexus, Amsinckia intermedia, AnaRallis
arvensis, Anthemis arvensis, Anthemis cotula, Atriplex
patula, Brassica ni~ra, Capsella bursa-pastoris,
Chenopodium album, Cirsium arvense, Datura stramonium,
Euphorbia helioscopia, Galeopsis tetrahit, Galium
aparine, Lamium amplexicaule, Lamium purpureum,
Matricaria inodora, Myosotis arvensis, Papaver rhoeas,
.
PlantaRo lanceolata, PolyRonum spp. (e.g. Poly~onum
aviculare, PolyRonum convolvulus and Poly~onum
persicaria), Portulaca oleracea, Raphanus raphanistrum,
13(~0915
-- 7 --
Senecio vulgaris, Sesbania florida, Sida spinosa,
Silene alba, Sinapis arvensis, Solanum ni~rum,
Stellaria media, Thlaspi arvense, Urtica urens,
Veronica hederifolia, Veronica Persica, Viola arvensis,
Xanthium spp. (e.g. Xanthium pennsylvanicwm and
Xanthium strumarium).
In accordance with usual practice, a tank mix may
be prepared prior to use by combining separate
formulations of the indi-~idual herbicidal components,
or separate formulations may be applied in a time-
separated manner.
The following greenhouse experiments illustrate the
present invention by demonstrating the synergistic
activity of of the phenoxyalkanoic acid herbicide MCPA
or CMPP and diflufenican in controlling the growth of
broad-leaf weed species.
EXPERIMENT 1
Greenhouse experiment showin~ the nature of biolo~ical
syner~ism between MCPA and diflufenican
A wide range of doses of MCPA, i.e. 125, 250, 500
and 1000 g a.e. (acid equivalent)/ha (in a composition
according to Example 2 as described hereinafter), and
of diflufenican, i.e. 31.25, 62,5, 125, 250 and 500
g/ha (in a composition according to Example 1 as
described hereinafter), were applied at a spray volume
of 290 l/ha to sets of four replicate 7,5 cm square
pots of-loam soil each planted with 4 Stellaria media
seedlings with 2-4 pairs of leaves or 3 Veronica
persica seedlings at the 2-4 leaf stage, After
13~)~9~5
_ 8 --
spraying, the pots were arranged in randomised blocks
in a greenhouse, watered as necessary, and assessed
after 14 days for percentage phytotoxicity (reduction
in green area compared with unsprayed plants)(0 = no
effect, 100 = complete destruction).
From these results the ED90 values (effective
dose giving 90% phytotoxicity) in grams of diflufenican
per hectare, for Stellaria media and Veronica persica,
were calculated for diflufenican alone and for
10 diflufenican with increasing rates of MCPA and for MCPA
alone.
The EDgo values for Stellaria media were as
follows:-
ED90
Diflufenican alone 995
Diflufenican with 125 g MCPA/ha 217
Diflufenican with 250 g MCPA/ha 134
Diflufenican with 500 g MCPA/ha 60
Diflufenican with 1000 g MCPA/ha 33
The EDgo value for MCPA alone was 1337 g a.e./ha;
~ 3 ~ 5
and the EDgo values for Veronica persica were:-
EDgo
Diflufenican alone 339
Diflufenican with 125 g MCPA/ha 135
Diflufenican with 250 g MCPA/ha 94
Diflufenican with 500 g MCPA/ha 52
Diflufenican with 1000 g MCPA/ha less then 32
The EDgo for MCPA alone was 1190 g a.e./ha.
The results were then used to plot isoboles with a
"two-sided effect" according to the methods of
P.M.L. Tammes, op. cit. The isoboles produced, shown
hereinafter in Figures I and II, were clearly type III
curves (Tammes, op. cit., page 75), characteristic of
synergi8m.
EXPERIMENT 2
Greenhouse experiment showin~ the nature of biolo~ical
synergism between C~PP and diflufenican
A wide range of dose~ of CMPP, i.e. 125, 250, 500
and 100 g a.e./ha (in a composition according to
Example 6 as described hereinafter), and of
diflufenican i.e. 31.25, 62.5, 125, 250 and 500 g/ha
(in a composition according to Example 1 as described
hereinafter) were applied at a spray volume of 290 l/ha
to sets of four replicate 7.5 cm square pots of loam
soil each planted with 4 Stellaria media plants with 6
leaves and just branching.
13~9~5
_ 10 -
After spraying the pots were arranged in randomised
blocks in a greenhouse, watered as necessary, and
assessed after 14 days for percentage phytotoxicity
(reduction in green area compared with unsprayed
plants) (0 = no effect, 100 = complete destruction).
From these results the EDgo values in grams
diflufenican per hectare for Stellaria media were
calculated for diflufenican alone and for diflufenican
with increasing rates of CMPP and for CMPP alone.
The ED90 values for Stellaria media were as
follows:-
EDgo
Diflufenican alone 454
Diflufenican with 125 g CMPP/ha 184
Diflufenican with 250 g CMPP/ha 88
Diflufenican with 500 g CMPP/ha 35
Diflufenican with 1000 g CMPP/ha less than 31
The EDgo for CMPP alone was 1135 g a.e./ha.
The results were then used to plo~ an isobole with
a "two-sided effect" according to the methods of
P.M.L. Tammes, op. cit. The isobole produced, shown
hereinafter in Figure III, was clearly a type III curve
(Tammes op. cit., page 75), characteristic of synergism.
~3C~915
- 11 -
According to a further feature of the present
invention, there is provided a product comprising
(a) a phenoxyalkanoic acid herbicide [preferably MCPA
or CMPP] or an agriculturally acceptable salt or ester
thereof, preferably a metal or amine salt or a
straight- or branched-chain alkyl ester thereof
containing from 1 to 10 carbon atoms in the alkyl
moiety which is optionally substituted by Cl_6-alkoxy
group(s), and (b) diflufenican as a combined
preparation for simultaneous, separate or sequential
use in controlling the growth of weeds at a cereal crop
locus.
According to a feature of the present invention,
there are provided compositions suitable for herbicidal
use comprising (a) a phenoxyalkanoic acid herbicide or
an agriculturally acceptable salt or ester thereof,
preferably a metal or amine salt or a straight- or
branched-chain alkyl ester thereof containing from 1 to
10 carbon atoms in the alkyl moiety which is optionally
substituted by Cl 6-alkoxy group(s), and (b)
diflufenican, for example in proportions of 100:1 to
1:2, preferably 20:1 to 1:2 for MCPA, 100:1 to 2:1 for
CMPP and 50:1 to 1:1 for R-CMPP, w/w in association
with, and preferably homogeneously dispersed in, a
herbicidally-acceptable diluent or carrier and/or
surface-active agent. Suitable diluents or carriers or
surface-active agents are of the type generally
13~(1 91S
- 12 -
accepted in the art as being suitable for use in
herbicidal compositions and which are compa~ible with
the phenoxyalkanoic acid herbicide and diflufenican.
The term "homogeneously dispersed" is used to include
compositions in which the phenoxyalkanoic acid
herbicide and diflufenican are dissolved in the other
components. The term "herbicidal compositions" is
used in a broad sense to include not only compositions
which are ready for use as herbicides but also
concentrates which must be diluted before use.
Preferably, the compositions contain from 0.05 to 90%
by weight of the phenoxyalkanoic acid herbicide and
diflufenican.
The herbicidal compositions may contain both a
diluent or carrier and a surface-active (e.g. wetting,
dispersing, or emulsifying) agent. Surface-active
agents which may be present in herbicidal compositions
of the present invention may be of the ionic or
non-ionic types, for example sulphoricinoleates,
products based on condensates of ethylene oxide with
nonyl- or octyl- phenols, or carboxylic acid esters of
anhydrosorbitois which have been rendered soluble by
etherification of the free hydroxy groups by
condensation with ethylene oxide, alkali and alkaline
earth metal salts or sulphuric acid esters and
sulphonic acids such as dinonyl- and dioctyl-sodium
sulphono-succinates and
130~91S
- 13 -
alkali and alkaline earth metal salts of high molecular
weight sulphonic acid derivatives such as sodium and
calcium lignosulphonates. Examples of suitable solid
diluents or carriers are aluminium silicate, talc,
calcined magnesia, kieselguhr, tricalcium phosphate,
powdered cork, adsorbent carbon black and clays such as
kaolin and bentonite. The solid compositions (which
may take the form of dusts, granules or wettable
powders) are preferably prepared by grinding the
phenoxyalkanoic acid herbicide and diflufenican with
solid diluents or by impregnating the solid diluents or
carriers with solutions of the pher.oxyalkanoic acid
herbicide and diflufenican in volatile solvents,
evaporating the solvents and, if necessary, grinding
the products so as to obtain powders. Granular
formulations may be prepared by absorbing the
phenoxyalkanoic acid herbicide and diflufenican
(dissolved in volatile solvents) onto the solid
diluents or carriers in granular form and evaporating
the solvents, or by granulating compositions in powder
form obtained as described above. Solid herbicidal
compositions, particularly wettable powders, may
contain wetting or dispersing agents (for example of
the types described above), which may also, when solid,
serve as diluents or carriers.
13C)~ 5
- 14 -
Liquid compositions according to the invention may
take the form of aqueous, organic or aqueous-organic
solutions, suspensions and emulsions which may incorp-
orate a surface-active agent. Suitable liquid
diluents for incorporation in the liquid compositions
include water, acetophenone, cyclohexanone, isophorone,
toluene, xylene and mineral, animal and vegetable oils
(and mixtures of these diluents). Surface-acti~e
agents, which may be present in the liquid compos-
itions, may be ionic or non-ionic (for example of the
types described above) and may, when liquid, also serve
as diluents or carriers.
Wettable powders and liquid compositions in the
form of concentrates may be diluted with water or other
suitable diluents, for example mineral or vegetable
oils, particularly in the case of liquid concentrates
in which the diluent or carrier is an oil, to give
compositions ready for use. When desired, liquid
compositions of the phenoxyalkanoic acid herbicide and
diflufenican may be used in the form of
self-emulsifying concentrates containing the active
substances dissolved in the emulsifying agents or in
solvents containing emulsifying agents compatible with
the active substances, the simple addition of water to
such concentrates producing compositions ready for use.
Liquid concentrates in which the diluent or carrier
is an oil may be used without further dilution using
the electrostatic spray technique.
.. . . . ... .. . . . . .. . ... . .. . .. ... . . . .. . . . . . . . . . . . .. . . ....
13~ 915
Herbicidal CQmpositiOnS according to the present
invention may also contain, if desired, conventional
adjuvants such as adhesives, protective colloids,
thickeners, penetrating agents, stabilisers;
sequestering agents, anti-caking agents, colouring
agents and corrosion inhibitors. These adjuvants may
also serve as carriers or diluents.
Preferred herbicidal compositions according to the
present invention are aqueous suspension concentrates
which comprise from 10 to 70% w/v of the
phenoxyalkanoic acid herbicide and diflufenican, from 2
to 10% w/v of surface-active agent, from 0.1 to 5% w/v
of thickener and from 15 to 87.9% by volume of water;
wettable powders which comprise from 10 to 90% w/w of
the phenoxyalkanoic acid herbicide and diflufenican,
from 2 to 10% w/w of surface-active agent and from 8 to
88% w/w of solid diluent or carrier; liquid water
soluble concentrates which comprise from 10 to 30% w/v
of the phenoxyalkanoic acid herbicide and diflufenican,
from 5 to 25% w/v of surface-active agent and from 45
to 85% by volume of water-miscible solvent, e.g.
dimethylformamide; liquid emulsifiable suspension
concentrates which comprise 10 to 70% w/v of the
phenoxyalkanoic acid herbicide and diflufenican, from 5
to 15% w/v of surface-active agent, from 0.1 to 5% w/v
of thickener and from 10 to 84.9% by volume of organic
13(~915
- 16 -
solvent; granules which comprise from 2 to 10% w/w of
the phenoxyalkanoic acid herbicide and diflufenican,
from O.S to 2% w/w of surface-active agent and from 88
to 97.5% w/w of granular carrier and emulsifiable
concentrates which comprise from 0.05 to 90% w/v, and
preferably from 1 to 60% w/v, of the phenoxyalkanoic
acid herbicide and diflufenican, from 0.01 to 10% w/v,
and preferably from 1 to 10% w/v, of surface-active
agent and from 9.99 to 99.94%, and preferably from ~9
to 98.99%, by volume of organic solvent.
Herbicidal compositions according to the present
invention may also comprise the phenoxyalkanoic acid
herbicide and diflufenican in association with, and
preferably homogeneously dispersed in, one or more
other pesticidally active compounds and, if desired,
one or more compatible pes~icidally acceptable diluents
or carriers, surface-active agents and conventional
adjuvants as hereinbefore described. Examples of
other pesticidally active compounds which may be
included in, or used in conjunction with, the
herbicidal compositions of the present invention
include herbicides, for example to increase the range
,
~3~`~915
- 17-
of weed species controlled, for example bifenox [methyl
5-(2,4-dichlorophenoxy)-2-nitrobenzoate]~
chlortoluron [N'-(3-chloro-4-methylphenyl)-N,N-
dimethylureal, cyanazine [2-chloro-4~ cyano-1-methyl-
ethylamino)-6-ethylamino-1,3,5-triazine], isoproturon
[N'-(4-isopropylphenyl)-N,N-dimethylurea], linuron
[N'-(3,4-dichlorophenyl)-N-methoxy-N-methylurea~,
methabenzthiazuron [N-(benzothiazol-2-yl)-N,N'-dimethyl-
urea~, hydroxybenzonitriles, e.g. ioxynil and
bromoxynil; insecticides, e.g. carbaryl ~naphth-l-yl
N-methylcarbamate] and synthetic pyrethroids, e.g.
permethrin and cypermethrin; and fungicides, e.g.
2,6-dimethyl-4-tridecyl-morpholine, methyl
N~ butylcarbamoylbenzimidazol-2-yl)carbamate,
1,2-bis-(3-methoxycarbonyl-Z-thioureido)benzene,
isopropyl l-carbamoyl-3-(3,5-dichlorophenyl)hydantoin
and 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-
l-yl)butan-2-one. Other biologically active materials
which may be included in, or used in conjunction with,
the herbicidal compositions of the present invention
are plant growth regulators, e.g.
(2-chloroethyl)trimethylammonium chloride and 2-chloro-
ethanephosphonic acid; and fertilizers containing, for
example, nitrogen, potassium and phosphorus and trace
elements known to be essential to successful plant
life, e.g. iron, magnesium, zinc, manganese, cobalt and
copper.
.. . . . .. . . .. . . .. . . . . . . . . .. ... . . . . .. .. . . . . . . .. . .. . ... . ..
. .
~3~)~915
_ 18 _
Pesticidally active compounds and other biolog-
ically active materials which may be included in, or
used in conjunction with, the herbicidal compositions
of the present invention, for example those
hereinbefore mentioned, and which are acids, may, if
desired, be utilized in the form of conventional
derivatives, for example alkali metal and amine salts
and esters.
The compositions of the invention may be made up as
an article of manufacture comprising the
phenoxyalkanoic acid herbicide and difl~fenican and
optionally other biologically active compounds as
hereinbefore described or, as is preferred, a
herbicidal composition as hereinbefore described, and
preferably a herbicidal concentrate which must be
diluted before use, comprising the phenoxyalkanoic acid
herbicide and diflufenican within a container for the
aforesaid phenoxyalkanoic acid herbicide and
diflufenican or a said herbicidal composition, and
instructions physically associated with the aforesaid
container setting out the manner in which the aforesaid
phenoxyalkanoic acid herbicide and diflufenican or
herbicidal composition contained therein is to be used
to control the growth of weeds. The containers will
normally be of the types conventionally used for the
storage of chemical substances which are solids at
normal ambient temperatures and herbicidal
compositions, particularly in the form of concentrates,
~3~:191S
- 19 -
for example cans and drums of metal, which may be
internally-lacquered, and plastics materials, bottles
of glass and plastics materials and, when the contents
of the container is a solid, for example granular
herbicidal compositions, boxes, for example of
cardboard, plastics materials and metal, or sacks.
The containers will normally be of sufficient capacity
to contain amounts of the active ingredients or
herbicidal compositions sufficient to treat at least
0.5 hectares of ground to control the growth of weeds
therein but will not exceed a size which is convenient
for conventional methods of har.dling. The
instructions will be physically associated with the
container, for example by being printed directly
thereon or on a label or tag affixed thereto. The
directions will normally indicate that the contents of
the container, after dilution if necessary, are to be
applied to control the growth of weeds at rates of
application from 125 g to 2500 g a.e. of the
phenoxyalkanoic acid herbicide and from 25 g to 250 g
of diflufenican per hectare in the manner and for the
purposes hereinbefore described.
13~J~915
- 20
The following Examples illustrate herbicidal
composi~ions according to the present invention.
EXAMPLE 1
An aqueous suspension concentrate was made from:
diflufenican 50% w/v
propylene glycol 5% w/v
Olin lOG (para-nonylphenoxy
polyglycidol~ 0.67% w/v
Soprophor FL ~triethanolamine
salt of oxyethylated
polyarylphenolphosphate) 1.33% w/v
Antifoam FD (silicone antifoam) 0.01% v/v
Rhodigel* 23 (xanthan gum) 0.2% w/v
dichlorophen sodium
solution, 40~ w/w 0.25% w/v
water to 100% by volume
by blending the diflufenican with an aqueous solution
of the Soprophor F~, Antifoam FD and Olin*lOG and
milling through a bead-mill. An aqueous solution of
the Rhodigel*23, dichlorophen sodium solution and
propylene glycol is then blended with the milled slurry
and made up to volume with water.
2S * trademark
~,!
`,
13QC~9~5
- 21 -
EXAMPLE 2
-
An aqueous solution containing potassium, sodium
and dimethylamine salts of MCPA equivalent to 500 g/l
of MCPA was formed by dissolving the potassium, sodium
and dimethylamine salts of MCPA in water.
EXAMPLE 3
An (1:20) emulsifiable concentrate was ormed from:-
diflufenican 2% w/v
MCPA as tbe isooctyl ester 40% w/v
Soprophor BSU (tristyryl phenol/
ethylene oxide condensate containing
18 moles of ethylene oxide) 3% w/v
Arylan*CA (calcium dodecyl benzene
sulphonate 70~/O solution in butanol)5% w/v
cyclohexanone 25% w/v
Solvesso*150 (aromatic C10 petroleum
fraction) to 100% by volume
by adding with stirring the diflufenican and MCPA
isooctyl ester to a solution of the Soprophor BSU andArylan*CA in the cyclohexanone. When fully dissolved,
Solvesso*150 is added to volume.
1.25 litres of the resulting formulation were
diluted in 200 litres of water and applied post-
emergence to 1 hectare of spring wheat to controlSinapis arvensis and Raphanus raphanistrum.
* trademark
:13()~915
- 22 -
EXAMPLE 4
A 1:2 mixture was formed by tank mixing 0.25 l of
the composition of Example 2 with 500 ml of the
composition of Example 1 in a volume of 200 1 of
water. The resulting spray fluid was applied to one
hectare of winter wheat to control Stellaria media and
Veronica ~ersica.
EXAMPLE 5
A 2:1 mixture was formed by tank mixing 877 ml of
the composition of Example 6 with 500 ml of the
composition of Example 1 in a volume of 200 1 of
water. The resulting spray fluid was applied to one
hectare of winter wheat to control Viola arvensis,
Veronica hederifolia and Galium aparine
EXAMPLE 6
An aqueous solution containing 570 g/l CMPP as the
potassium salt was formed by dissolving the CMPP
potassium salt in water.
EXAMPLE 7
A 100:1 mixture was formed by tank mixing 4386 ml
of the composition of Example 6 with 50 ml of the
composition of Example 1 in a volume of 500 l/ha. The
resulting spray fluid was applied to one hectare of
winter barley to control Stellaria media, Galium
aparine and Viola arvensis.
In the mixed formulations in the Examples described
hereinbefore, the phenoxyalkanoic acid herbicide ma~ be
replaced by the appropriate quantities of othet
phenoxyalkanoic acid herbicides.
13~09~5
- 23
¢;~CONH~F
0 ~ 1
1 ~" II
R2~0-A-COOH
